Hitherto, it has already been known that certain 1,2,4-triazol-5-one derivatives and tetrazolinone derivatives have herbicidal and fungicidal activities, as described below.
For example, the known 1,2,4-triazol-5-one derivatives include such compounds as described in literatures (1) to (4) below.
(1) Japanese patent application first publication (Kokai) No. Hei-7-76578 describes a compound represented by the general formula (A) ##STR2## wherein X denotes oxygen atom or sulfur atom, R.sub.1 denotes a haloalkyl group, R.sub.2 denotes a cycloalkyl group, a cycloalkylalkyl group and so on, R.sub.3 denotes hydrogen atom or a halogen atom, R.sub.4 denotes nitrile group or nitro group and R.sub.5 denotes a halogen atom or a heterocyclic alkoxy group and so on.
(2) Japanese patent application first publication (Kokai) No. Hei-3-106865 describes a compound represented by the general formula (B) ##STR3## wherein R.sub.1 denotes a cycloalkyl group, a phenylalkyl group, a halogen atom, an aminocarbonyl group substituted with a substituted phenyl group, and so on; R.sub.2 denotes hydrogen atom or a lower alkyl group; and R.sub.3 denotes a halogen atom, an alkyl group and so on.
(3) Japanese patent application first publication (Kokai) No. Sho-64-29368 describes a compound represented by the general formula (C) ##STR4## wherein X and Y denote oxygen atom or sulfur atom, R.sub.1 denotes hydrogen atom and so on, R.sub.2 denotes an unsubstituted or substituted phenyl group, an aralkyl group and so on, and R.sub.3 and R.sub.4 denote hydrogen atom, an alkyl group or an unsubstituted or substituted aryl group and so on.
(4) Japanese patent application first publication (Kokai) No. Hei-6-293744 describes a compound represented by the general formula (D) ##STR5## wherein R.sub.1 denotes hydrogen atom and so on; R.sub.2 denotes ##STR6## in which R.sub.6 and R.sub.7 denote an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group and so on; R.sub.3 denotes hydrogen atom, an alkyl group, a haloalkyl group and so on; R.sub.4 denotes hydrogen atom and so on; and R.sub.5 denotes amino group or hydroxy group and so on.
Furthermore, various 1,2,4-triazol-5-one derivatives have been described in the following literatures (5) to (24), namely (5) Japanese patent application first publication (Kokai) No. Sho-56-32403; (6) Japanese patent application first publication (Kokai) No. Sho-56-53663; (7) Japanese patent application first publication (Kokai) No. Sho-56-53662; (8) Japanese patent application first publication (Kokai) No. Sho-58-23680; (9) U.S. Pat. No. 4,705,557; (10) PCT international publication No. WO85/01637; (11) PCT international publication No. WO86/02642; (12) U.K. patent No. 2230261 specification; (13) Japanese patent application first publication (Kokai) No. Hei-3-106865; (14) German patent No. 4437049; (15) German patent No.4435476; (16) German patent No. 4431219; (17) U.S. Pat. No. 5,035,740 specification ; (18) Japanese patent application first publication (Kokai) No. Hei-3-181472; (19) German patent No. 3920414; (20) Japanese patent application first publication (Kokai) No. Hei-3-17070; (21) South African patent No. 8805308; (22) Japanese patent application first publication (Kokai) No. Sho-64-29368; (23) Japanese patent application first publication (Kokai) No. Sho-63-255271; and (24) Japanese patent application first publication (Kokai) No. Sho-52-118471.
However, the above-mentioned literatures (1) to (24) do not describe any 1,2,4-triazol-5-one derivatives having carbamoyl group at the 4-position thereof.
Furthermore, for the tetrazolinone derivatives there have been known such compounds as described in literatures (25) to (50) below.
(25) Japanese patent application first publication (Kokai) No. Sho-62-12767 describes a compound represented by the general formula (E) ##STR7## wherein R denotes a cycloalkyl group, phenyl group, naphthyl group and so on, R.sub.1 and R.sub.2 may be the same or different and each denote a C.sub.1 -C.sub.6 alkyl group, a C.sub.5 -C.sub.6 alkenyl group, a C.sub.5 -C.sub.6 cycloalkyl group, a C.sub.7 -C.sub.9 aralkyl group, or phenyl group which may be substituted with a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 haloalkyl group or a C.sub.1 -C.sub.6 alkoxy group and so on.
In addition, the known tetrazolinone derivatives include such compounds as described in (26) Japanese patent application first publication (Kokai) No. Sho-60-146879; (27) Japanese patent application first publication (Kokai) No. Hei-5-331154; (28) Japanese patent application first publication (Kokai) No. Hei-5-339249; (29) Japanese patent application first publication (Kokai) No. Hei-5-331153; (30) Japanese patent application first publication (Kokai) No. Hei-6-306061; (31) Japanese patent application first publication (Kokai) No. Hei-6-199818; (32) Japanese patent application first publication (Kokai) No. Hei-7-258230; (33) Japanese patent application first publication (Kokai) No. Hei-8-81459; (34) Japanese patent application first publication (Kokai) No. Hei-8-99975; (35) Japanese patent application first publication (Kokai) No. Hei-8-119947; (36) Japanese patent application first publication (Kokai) No. Hei-8-119948; (37) Japanese patent application first publication (Kokai) No. Hei-8-119950; (38) Japanese patent application first publication (Kokai) No. Hei-8-119951; (39) Japanese patent application first publication (Kokai) No. Hei-8-225547; (40) Japanese patent application first publication (Kokai) No. Hei-8-311048; (41) Japanese patent application first publication (Kokai) No. Hei-8-259549;
(42) U.S. Pat. No. 4,830,661 specification; (43) U.S. Pat. No. 4,956,469 specification; (44) U.S. Pat. No. 5,003,075 specification; (45) U.S. Pat. No. 5,019,152 specification; (46) Portuguese patent No. 101563 specification; (47) Japanese patent application first publication (Kokai) No. Hei-8-119949; (48) Japanese patent application first publication (Kokai) No. Hei-8-259548; (49) U.S. Pat. No. 5,136,868 specification; and (50) PCT international publication No. WO85/01939.
In the development of the herbicide, it is an important subject to create such new herbicidal compounds which exhibit a selective herbicidal activity owing to that some differences occur between the sensitivity of crop plants, namely useful cultivated plants and the sensitivity of weeds against a herbicide, and so on. However, when certain herbicidal compounds exhibit a phytotoxicity to the crop plants even if they have a high herbicidal activity, it is hard to say that such herbicidal compounds can be used satisfactorily as the herbicide in practice. Thus, it is now demanded to develop such new herbicidal compounds which is free from the drawbacks mentioned above. In this view, the above-mentioned 1,2,4-triazol-5-one and tetrazolinone derivatives which are known compounds are not necessarily a satisfactory herbicide. Accordingly, it is an object of this invention to provide, in place of the above-mentioned known herbicidal compounds, such new 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives which have an excellent herbicidal activity and show very low phytotoxicity to the crop plants and hence have a safety to the crop plants when used as the herbicide. It is another object of this invention to provide a herbicide comprising such new 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives as an active ingredient.